06655
(R)-(−)-1-Aminoethylphosphonic acid
≥97.0% (NT)
Synonym(s):
L-(−)-1-Aminoethylphosphonic acid, L-Ala(P)
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About This Item
Linear Formula:
CH3CH(NH2)P(O)(OH)2
CAS Number:
Molecular Weight:
125.06
Beilstein/REAXYS Number:
4291032
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22
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assay
≥97.0% (NT)
optical activity
[α]20/D −4.8±0.5°, c = 5% in H2O
storage temp.
2-8°C
SMILES string
C[C@H](N)P(O)(O)=O
InChI
1S/C2H8NO3P/c1-2(3)7(4,5)6/h2H,3H2,1H3,(H2,4,5,6)/t2-/m1/s1
InChI key
UIQSKEDQPSEGAU-UWTATZPHSA-N
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General description
(R)-(-)-1-Aminoethylphosphonic acid is a synthetic analog of L-alanine that shows antibacterial property.
Application
(R)-(−)-1-Aminoethylphosphonic acid can be used to prepare copper(II) heteroligand complexes, which are employed in the solution equilibrium studies.
Other Notes
Di- to tetrapeptides with this amino acid analogue at the "P-terminal" are bactericides and synergistic potentiators of penicillins and cephalophorins.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Reaction of Alanine Racemase with 1-Aminoethylphosphonic Acid Forms a Stable External Aldimine
Stamper CGF, et al.
Biochemistry, 37(29), 10438-10445 (1998)
Stabilities and coordination modes of α-alaninephosphonic acid in copper (II) heteroligand complexes with ethylenediamine, diethylenetriamine or N, N, N′, N′, N″-pentamethyldiethylene triamine in aqueous solution
Kamecka A, et al.
Journal of Solution Chemistry, 40(6), 1041-1054 (2011)
J G Allen et al.
Antimicrobial agents and chemotherapy, 16(3), 306-313 (1979-09-01)
The metabolism and pharmacokinetics of a synthetic antibacterial phosphonodipeptide, alafosfalin, have been studied in rats, baboons, and human volunteers. The compound was rapidly absorbed from the injection site after subcutaneous and intramuscular administration and gave peak plasma concentrations at 15
F R Atherton et al.
Antimicrobial agents and chemotherapy, 15(5), 677-683 (1979-05-01)
Peptide mimetics with C-terminal residues simulating natural amino acids have been designed as inhibitors of bacterial cell wall biosynthesis. The phosphonopeptide series consisting of various l and d residues of natural amino acids combined with 1-aminoalkyl (and aryl-alkyl-) phosphonic acid
D A Mironenko et al.
Biokhimiia (Moscow, Russia), 55(6), 1124-1131 (1990-06-01)
Penicillin acylase from E. coli (EC 3.5.1.11) was found to hydrolyze N-phenylacetylated 1-aminoethylphosphonic acid and its esters. The enzyme preferentially converts the R-form of the substrates: the ratios of the bimolecular rate constants of penicillin acylasecatalyzed hydrolysis of R- and
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